Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides |
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| Authors: | Mitsuru Shindo Tomoyuki Sugioka Kozo Shishido |
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| Institution: | Institute of Health Biosciences, The University of Tokushima Graduate School, Sho-machi 1, Tokushima 770-8505, Japan |
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| Abstract: | The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF3 mediated lithium acetylide provided either the α- or β-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the β- and α-products, respectively. |
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| Keywords: | Oxirane Alkynylation Regioselectivity Electronic effect Lewis acid |
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